1,2-Dibromoethane → HCID 14150224, compound

HRID 648800Notes

Reaction equation

HRID 648800 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:16])[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:4]([F:17])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:25][CH2:26]Br>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:10]2([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:26][CH2:25]2)=[O:16])=[C:4]([F:17])[CH:3]=1

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 20145884HCID 20145884, compound

Product 1

HCID 14150224HCID 14150224, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a manner similar to the procedure described in Example B, 31.0 grams (119.0 mmol) of ethyl 3-[(4-chloro-2-fluorophenyl)amino]-3-oxopropanoate, 41.4 grams (300.0 mmol) of anhydrous potassium carbonate, 100 milliliters anhydrous dimethylformamide and 10.4 milliliters (120.0 mmol) of 1,2-dibromoethane were reacted for a period of 3 days to give 20.6 grams (72.0 mmol) of ethyl 1-(4-chloro-2-fluorophenylaminocarbonyl)cyclopropanecarboxylate as a colorless solid having a melting point of 94.0° C.-95.5° C. The total yield was 61 percent. NMR analysis of the product indicated the following:

Workup

  1. customwere reacted for a period of 3 days

Sources & evidence

ORD record
ord-1ffbeb5bd4cf499cb847d095a694bee3
Source dataset
uspto-grants-1988_04
Patent number
US04736056

Reaction notes

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